4-Benzyloxyphenylacetic acid → 2-Oxo-2-(pyridin-4-yl)ethyl 2-(4-(benzyloxy)phenyl)acetate

HRID 446793Notes

Reaction equation

HRID 446793 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([OH:18])=[O:17])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].Br.Br[CH2:27][C:28]([C:30]1[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=1)=[O:29]>CO>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][C:16]([O:18][CH2:27][C:28](=[O:29])[C:30]2[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=2)=[O:17])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 810334-Benzyloxyphenylacetic acidHCID 27762394-(Bromoacetyl)pyridine hydrobromideHCID 23665647Potassium tert-butoxide2×

Product 1

HCID 673017532-Oxo-2-(pyridin-4-yl)ethyl 2-(4-(benzyloxy)phenyl)acetateYield 49.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a 10° C. stirred solution of 2-(4-(benzyloxy)phenyl)acetic acid (5.0 g, 0.02 mol) in MeOH (50 mL) was added a solution of potassium tert-butoxide (2.43 g, 0.02 mol) in MeOH (50 mL) under an inert atmosphere. The reaction mixture was stirred for 1 h, concentrated in vacuo and the residue was dissolved in DMF (30 mL). Potassium tert-butoxide (3.6 g, 0.03 mmol) was then added followed by 2-bromo-1-(pyridin-4-yl)ethanone hydrobromide (10.3 g, 0.05 mol), and the reaction mixture at RT. The reaction mixture was then stirred for an additional 16 h at RT, quenched with water, stirred for an additional 10 min and the precipitated solid was filtered. The crude solid was dissolved in EtOAc (200 mL) and washed with water, dried over Na2SO4, filtered and concentrated in vacuo to afford 2-oxo-2-(pyridin-4-yl)ethyl 2-(4-(benzyloxy)phenyl)acetate (3.6 g, 48%) as a solid.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionthe residue was dissolved in DMF (30 mL)
  3. customat RT
  4. stirringThe reaction mixture was then stirred for an additional 16 h at RT
  5. customquenched with water
  6. stirringstirred for an additional 10 min
  7. filtrationthe precipitated solid was filtered
  8. dissolutionThe crude solid was dissolved in EtOAc (200 mL)
  9. washwashed with water
  10. dry with materialdried over Na2SO4
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ba2be6a703024eb5aa31bbd4d9aa17b6
Source dataset
uspto-grants-2013_07
Patent number
US08481534B2

Reaction notes

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